177080-67-0

Basic information

• Product Name: 2-Methyl-2-adamantylmethacrylate
• Synonyms: 2-methacryloyloxy-2-methyladamantane;2-Methyl-2-adamantyl methacrylate;2-Methacryloyloxy-2-MethyladaMantane (stabilized with MEHQ);2-Methyl-2-adamantyl Methacrylate Methacrylic Acid 2-Methyl-2-adamantyl Ester;2-Methyl-2-adaMantyl Methacrylte;2-MethyladaMantan-2-yl Methacrylate
• CAS NO: 177080-67-0
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.33
• Product Categories: We have in stock now.
• Mol File: 177080-67-0.mol

Chemical Properties

• Boiling Point: 301.311 °C at 760 mmHg
• Flash Point: 120°C(lit.)
• Appearance: /
• Density: 1.061 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.5050 to 1.5090
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Methyl-2-adamantylmethacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-2-adamantylmethacrylate(177080-67-0)
• EPA Substance Registry System: 2-Methyl-2-adamantylmethacrylate(177080-67-0)

Safety Data

• Hazardous Substances Data: 177080-67-0(Hazardous Substances Data)

Usage

Synthesis

The synthesis of?2-Methyl-2-adamantylmethacrylate is as follows:Add 3546ml of n-heptane in the 5L four-necked flask equipped with stirring paddle, condenser tube and thermometer, turn on stirring, add 126.3g of 2-methyladamantanol to the system, and slowly add 0.022g polymerization inhibitor tetrachlorobenzoquinone to the reaction, add 110.8g basic ion exchange resin, adjust pH=7-8, cool down to -13°C, slowly add 110.8g vinyl methacrylate dropwise to the reaction system, keep the reaction for 7h, monitor the reaction progress, and take samples for detection After the reaction was completed, 1000 ml of water was added to the reaction system, and the mixture was stirred and extracted for phase separation. The organic phase was dried, concentrated under reduced pressure and evaporated to dryness to obtain 167 g of 2-methyl-2-adamantyl methacrylate product with a yield of 93.78%.

InChI:InChI=1/C15H22O2/c1-9(2)14(16)17-15(3)12-5-10-4-11(7-12)8-13(15)6-10/h10-13H,1,4-8H2,2-3H3

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Relevant articles and documents

Method for synthesizing adamantyl (meth) acrylate

The invention discloses a method for synthesizing adamantyl (meth) acrylate, and relates to the field of organic synthesis. The method for synthesizing adamantyl (meth) acrylate comprises the steps: 1, reacting (methyl) acrylic acid with alkyl sulfonyl chloride to generate mixed anhydride S1; 2, reacting 2-adamantanone with halogenated alkane under the action of a lithium reagent or a Grignard reagent to generate an intermediate S2; and 3, reacting the mixed anhydride S1 with the intermediate S2 to generate the adamantyl (meth) acrylate. The invention provides a synthetic method of adamantyl (meth) acrylate, and provides more selectivity for synthesis of adamantyl (meth) acrylate. The synthesis method disclosed by the invention is high in yield, high in product purity and low in synthesis cost.

Process for Producing 2-Methyladamantan-2-Yl (Meth)Acrylate and 2-Methyladamantan-2-Yl (Meth)Acrylate

An object of the present invention is to provide a process for purifying 2-methyladamantan-2-yl(meth)acrylate with high separation efficiency and an industrially advantageous preparation process of 2-methyladamantan-2-yl(meth)acrylate. The present invention pertains to a preparation process of 2-methyladamantan-2-yl(meth)acrylate which comprises reacting 2-methyleneadamantane and (meth)acrylic acid by an acid catalyst to obtain a reaction mixture, and then separating 2-methyleneadamantane from the reaction mixture to obtain 2-methyladamantan-2-yl(meth)acrylate, wherein the reaction mixture is distilled in the presence of an organic compound having a boiling point, under atmospheric pressure, of 150° C. or greater but not greater than 260° C.

Adamantyl ester monomer composition

The present invention discloses an adamantyl ester monomer composition characterized by containing at least an adamantyl ester monomer having at least one polymerizable unsaturated bond in the molecule, and a compound represented by the following general formula (1): (in the formula, R1 is an alkyl group of 1 to 5 carbon atoms, R2 is an alkyl group of 1 to 5 carbon atoms, R3 is a hydrogen atom or an alkyl group of 1 to 5 carbon atoms, and R4 is a hydrogen atom or a methyl group). The composition has high storage stability and, by subjecting it to distillation, an adamantyl ester monomer of high purity can be obtained easily.

ADAMANTYL ESTER MONOMER COMPOSITION

The present invention discloses an adamantyl ester monomer composition characterized by containing at least an adamantyl ester monomer having at least one polymerizable unsaturated bond in the molecule, and a compound represented by the following general formula (1): (in the formula, R1 is an alkyl group of 1 to 5 carbon atoms, R2 is an alkyl group of 1 to 5 carbon atoms, R3 is a hydrogen atom or an alkyl group of 1 to 5 carbon atoms, and R4 is a hydrogen atom or a methyl group). The composition has high storage stability and, by subjecting it to distillation, an adamantyl ester monomer of high purity can be obtained easily.

PROCESS FOR PRODUCING (METH)ACRYLIC ANHYDRIDE AND PROCESS FOR PRODUCING (METH) ACRYLIC ESTER

(Meth)acrylic acid is reacted with a fatty acid anhydride and the resultant reaction mixture is neutralized and washed with an aqueous alkaline solution having a pH of 7.5 to 13.5. Thus, high-purity (meth)acrylic anhydride can be industrially advantageously produced while avoiding polymerization. This (meth)acrylic anhydride is reacted with a secondary or tertiary alcohol in the presence of a basic compound which in 25° C. water has an acidity (pKa) of 11 or lower. Thus, a high-purity (meth)acrylic ester can be produced in high yield.

Processes for preparation of 2-alkyl-2adamantyl esters

A magnesium halide salt of a 2-alkyl-2-adamantanol is reacted with a carboxylic acid halide such as acrylic chloride or the like in the presence of a tertiary amine to produce a 2-alkyl-2-adamantyl ester (the first invention). A 2-alkyl-2-adamantanol is reacted with a carboxylic acid such as acrylic acid or the like in the presence of an acid catalyst such as concentrated sulfuric acid or the like and a drying agent composed of an acidic or neutral inorganic compound (e.g. magnesium sulfate) which is a solid at ordinary temperature in a dried state or of a water-absorbing high-molecular compound, to produce a 2-alkyl-2-admantyl ester (the second invention). The above ester is important as a raw material for a resist for semiconductor production.

Process for the preparation of alicyclic ketones and an alkyl-substituted alicyclic esters

A high-purity alicyclic ketone which is a raw material for an alkyl-substituted alicyclic ester such as an alkyl adamantyl ester compound which is useful as a resist raw material can be obtained by a simple operation such as extraction without a special purification step such as distillation or recrystallization. In this process, when an alicyclic hydrocarbon is oxidized with concentrated sulfuric acid or fuming sulfuric acid, the reaction solution after oxidation is poured into water and a solid is extracted with an organic solvent, the concentration of sulfuric acid in the water layer at the time of extraction is adjusted to 60 to 90 wt % to carry out extraction so as to obtain an alicyclic ketone.

Process for preparing acrylate compound

An acrylate compound of formula (4): 1is produced by allowing an acrylic acid compound of formula (1): 2to react with an unsaturated compound of formula (2) or (3): 3In formulae (1) through (4), R1 and R2 are H or F, R3 is H, F, or an alkyl, alkenyl, fluoroalkyl or fluoroalkenyl group, R4 and R5 are H, halogen, or an alkyl, alkenyl, halogenated alkyl or halogenated alkenyl group; and X and Y are an unsubstituted or substituted hydrocarbon group, and dashed line - - - - - means that X and Y may be bonded together to form a cyclic structure.

Process of the preparation of high-purity alkyladamantyl esters

There is provided a method for obtaining an alkyladamantyl ester efficiently by distilling and purifying a crude alkyladamantyl ester containing impurities which decompose the alkyladamantyl ester without decomposing the alkyladamantyl ester. The crude alkyladamantyl ester such as crude 2-methyl-2-adamantyl methacrylate is distilled in the presence of a heterocyclic compound and/or a basic compound such as 3-ethyl-3-hydroxymethyloxetane or diglycidyl bisphenol A.

Production of 2-hydrocarbyl-2-adamantyl acrylate compounds

A 2-hydrocarbyl-2-adamantyl acrylate compound represented by the following Formula 6: is produced easily and stably with high yields by reacting a 2-adamantanone compound represented by the following Formula 1: with at least one organometallic compound represented by the following Formula 2 or 3:R1MgXR1Li and at least one acrylic compound represented by the following Formula 4 or 5: wherein, R1, R2, R3, X, Y and n in the above formulae being as defined in the disclosure.